Sorry, can't get past this part, how do you reef without pointing into the wind ?

Jeff beat me to it, but since you are asking.

My boat is a 38 feet boat with main sail area of 34 m2 (368 sq feet), inline spreaders, two line reef setup, lazy bag and a rigid vang.
The mast (or tack) reef line is attached to a ring in the sail and is led back to the cabin top winch. The clew ref line is a standard setup going to the opposite cabintop winch (alternate side's for each reef).

But this technique works on other boats also. We did this on a Hanse 470 (with swept spreaders and single line reef) a week ago while sailing upwind in a race (At one of the owners amazement - he wanted to head into the wind for reefing while racing)

We can do this at most point's of sail except DDW, you must not sail so deep that the sail will hang on the spreaders during the operation.

Here is the procedure.

Put or keep the boat on a course where you can do the maneuver and have sufficient room/time to complete (preferably on starboard tack

Tighten the topping lift (If you don't have a rigid vang)

Ease the main sheet a little to take pressure off the sail.

Ease the kicker so the boom have room to lift

Slack the main halyard to preset mark (if no mark you must take it in increments - don't ease to much)

Use the winch to haul in the tack (mast) reef line

Use the winch to haul in the clew reef line

(If you have single line reef only one line but more rope)

You should not need to touch the halyard any more

Sheet in

Tighten kicker (if needed)

Clear up all the lines

Finished

My boat is tracking so good that i can do this singlehanded w/o any use of autopilot or engine, everything is done from the cockpit close to wheel and winches.

I prefer this method because
I get a more stable platform to work on than a boat bobbing on the waves
Don't loose much headway while doing it